Potassium Carbonate → (R)-3'-(Thiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

HRID 2109424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2109424
[O:1]1[C@@:5]2([CH:10]3[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]3)[CH2:6]2)[CH2:4][NH:3][C:2]1=[O:13].Br[C:15]1[S:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I>[S:19]1[CH:15]=[CH:16][CH:17]=[C:18]1[N:3]1[CH2:4][C@:5]2([CH:10]3[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]3)[CH2:6]2)[O:1][C:2]1=[O:13]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 138512-BromothiopheneHCID 5310971AR-R-17779

Produkt 1

HCID 9921468(R)-3'-(Thiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-oneAusbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator

Versuchsvorschrift

(S)-Spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one (505 mg, 3.58 mmol), 5-bromothiophene (1.75 g, 10.74 mmol), copper (I) iodide (69 mg, 0.36 mmol) and potassium carbonate (495 mg, 3.58 mmol) were stirred at 120° C. overnight. After cooling to room temperature, the mixture was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give the title compound as a yellow solid (450 mg), m/zz 265 (MH+).

Aufarbeitung

  1. customthe mixture was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b5f6e47d584b469d8e8a8a9ce697ddd2
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514567B2

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